It's not that hard to see what Neil was intending for abducting Winter.
Then again, in every contest, there should be a prize for the winner, and apparently, the Middleton family has come up with quite a huge reward for the marriage interview candidate who'll emerge victorious in the end - that is their heiress' hand in marriage and a great sum of money. The goal is either to make her fall or gain her permission to be wed. However, as if starting this competition without informing her is not enough to violate her rights and freedom to decide, there are also no rules as to how they should woo her.